CEO
Michael George Rosenbaum, also known as Mike Rosenbaum, is the Chief Executive Officer and Director of Guidewire Software, Inc. (GWRE), a position he has held since August 2019.[[1]](https://app.boardroomalpha.com/profiles/people/A1114038-MICHAEL_GEORGE_ROSENBAUM)[[2]](https://www.gurufocus.com/insider/90239/michael-george-rosenbaum)[[3]](https://simplywall.st/stocks/us/software/nyse-gwre/guidewire-software/management) Aged 54, he owns approximately 236,743 to 237,268 shares of GWRE stock, valued at around $38-56 million as of mid-2025, representing about 0.18-0.2% ownership.[[2]](https://www.gurufocus.com/insider/90239/michael-george-rosenbaum)[[3]](https://simplywall.st/stocks/us/software/nyse-gwre/guidewire-software/management)[[4]](https://www.marketbeat.com/instant-alerts/guidewire-software-nysegwre-ceo-michael-george-rosenbaum-sells-1200-shares-2026-01-15/) His total yearly compensation is approximately $14.01 million, primarily from bonuses, stock, and options.[[3]](https://simplywall.st/stocks/us/software/nyse-gwre/guidewire-software/management)
Rosenbaum has recently engaged in multiple share sales under a pre-arranged 10b5-1 trading plan, including 1,200 shares on January 13, 2026, at $180.87 (totaling $217,044), leaving him with 236,743 shares valued at about $42.8 million, as well as prior sales in late 2025 totaling over 19,000 shares.[[4]](https://www.marketbeat.com/instant-alerts/guidewire-software-nysegwre-ceo-michael-george-rosenbaum-sells-1200-shares-2026-01-15/)[[5]](https://www.investing.com/news/insider-trading-news/guidewire-software-ceo-rosenbaum-sells-286k-in-shares-93CH-4424866)[[6]](https://www.stocktitan.net/sec-filings/GWRE/form-4-guidewire-software-inc-insider-trading-activity-1696d74c5d2b.html) He also serves as a Director at DocuSign, Inc. since September 2025.[[3]](https://simplywall.st/stocks/us/software/nyse-gwre/guidewire-software/management) Guidewire Software develops cloud-based software for property and casualty insurance carriers, including its InsuranceSuite products for policy administration, billing, and claims management.[[4]](https://www.marketbeat.com/instant-alerts/guidewire-software-nysegwre-ceo-michael-george-rosenbaum-sells-1200-shares-2026-01-15/)
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